Amids of the arylalkyloxyacetic acids and process of making same.



. M 5 1s a srnrs earner canton.

ERNST IPREISWERK AND WALTER BERNOULLI, OF BASED, SWITZERIIAND; ASSIGNORS TO SOCIETY OF CHEMICAL INDUSTRYIN BASLE, OF BASEL, SWITZERLAND.

AMIDS OF THE ARYLALKYLOXYACE'JZIG ACIDS AND PROCESS OF MAKING No Drawing.

Specification of Letters Patent.

Application filed October 24, 1912.

Patented Mayo, 119.313.

Serial No.'727,594.

To all 'vhom 66 may concern:

Be it known that we, ERNST PREISWERK, doctor of philosophy and chemist, and WALTER BERNoULL'I, doctor of philosophy and chemist, .bot-h citizens of the Swiss public, and residents of Basel, Switzerland, have invented new and useful Amids of the Arylalkylo'xyacetic Acids and a Process of Making Same, of which the following is a full, clear; and exact specification.

We have found that thetill now unknown amids of the arylalkyloxyacetic acids, corresponding to the general formula (wherein m and y stand for hydrogen or alkyl), have besides of a very small poisonous action valuable hypnotic and sedative properties. As these properties of the said compounds are considerably reinforced'comparatively to the corresponding derivatives of phenylglycolic acid, an essential influence is attributed to the presence of the alkyloxy, group.

Thenew compounds are diflicultly soluble in water, ligroin and petroleum ether and easily soluble in alcohol and benzene. They are prepared by treating the esters of aryl alkyloxyacetic acids of the general formula 12: Aryl-C C0.b.Alkyl 0-Alkyl with a basic compound having the radical NH as for instance ammonia and primary or secondary amins.

The esters employed as parent material may be prepared by the action of sodium' alcoholates on the esters of arylchloroacetic acids (Comp. R. Meyer and H. Bonder, Lz'ebz'gs Annalen 220 pag. 44/45) or by treating the correspondin derivatives of phenylglycolic acid with al lhaloides in presence of silver oxid (Comp. McKennie, J o'umzal of the Chemical Society of London, 75, pag. 755 and fol.).

Example 1:1 part of ethylester of phenylethoxyacetic acid (boiling at 145 to 147 C.

under a pressure of 20 millimeters) is agitated with 10 parts of a saturated aqueous solution of ammonia for several hours at ordinary temperature. By evaporation of the ammonia, the phenylethoxyacetamid cam-og omen separates from the liquid in the form of colorless needles. This amid is easily soluble in alcohol and benzene, somewhat 'less soluble. in ether and more diflicultly soluble in ligroin,-petroleum-ether and water.

In an analogous manner canbe prepared (1) from the ethylester of phenylmethoxyacetic acid (boiling'at 148 to 151 C. under a pressure of 22 millimeters) the phen lmethoxyacetamid melting at 110 to 111 4 (2) from the ethylester of paratolylethoxyacetic acid (boiling at 160 to 165 C. under a pressure of. '22 millimeters) the paratolylethoxyacetamid melting at 130 to 131 (1; (3') from the ethylester of phenylal-- lyloxyacetic acid (boiling at 163 to 164 C.

under a pressure of 24 millimeters) the limeters a liquid boiling at 181 to 189 C. is.

distilled oil", which. becomes quickly solid. From petroleum ether crystallizes the phenyloxypropolyl acetmonoethylamid.

can-on O.NH.G- H5 in the form of colorless needles melting at 51 C. It dissolves easily in alcohol and benzene, more difiicultly in petroleum ether 1 and ligroin and very diificultly in'water.

What we claim is:

1. The herein described process for the manufacture of amids of the arylalkylo'xyac'etic acids consisting in treating the ester of the formula.

0.0.A1ky1 0.1mm

witN-hHa basic compound having the radical 2. 'l he herein described process for the manufacture of amids of the pl enylalkyloxyacetic acids, consisting in treating the, ester of the formula 7H CaHtC C0.0.Alky1 QAlkyl I with a basic compound having theradical -NH Aryl--C 3. The herein described process for the Aryl-C acetic acids, consisting in treating the ester of the formula with ammonia.

5. The herein described process for the manufacture of phenylethoxyacetamid consisting in treating the ethylester of phenylethoxyacetic acid H C sHu*C CO.O-C Hn with ammonia. I

6. As new products thedescribed amids of the arylalkyloxyacetic acids, corresponding to the formula O.Alky1 Anyl-C H comm having hypnotic and sedative properties, diflicultly soluble in water, petroleum ether and'ligroin and easily soluble in alcohol and benzene. I

7. As a new article of manufacture, the described phenylethoxyacetamid corresponding to the formula cum- 21 cone:

crystallizing from water in colorless needles melting'at 90 (1., easily soluble in alcohol and benzene, diificultly soluble in petroleum Y ether, ligroin and water and having Valuable hypnotic and sedative roperties.

In witness whereof we have hereunto signed our names this 12 day of October 1912, in the presence of two subscribing witnesses.

ERNST PREISWERK. WALTER BERNOULLI.

Witnesses I Geo. Gmono, Amman BRAUN. 

